


A Successful Winchester Vacation

by NaughtyPastryChef



Category: Supernatural
Genre: Blow Jobs, Bottom Sam, Case Fic, Coitus Interruptus, Dirty Talk, M/M, Top Dean, set in season 5
Language: English
Status: Completed
Published: 2016-05-06
Updated: 2016-05-06
Packaged: 2018-06-01 03:39:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,474
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6499336
Author URL: https://archiveofourown.org/users/NaughtyPastryChef/pseuds/NaughtyPastryChef
Summary: <blockquote class="userstuff">
              <p>My entry for the 2016 Wincest Reverse Bang. Art by the wonderful stormbrite.<br/>The apocalypse is coming and they can’t stop it, but that doesn’t mean that they can’t take just a few days, right? All they want is a little calm and privacy in the midst of chaos.</p>
            </blockquote>





	A Successful Winchester Vacation

**Author's Note:**

> Oh, this was so much fun! Love to stormbrite, who was a pleasure to collaborate with, and the link to her amazing art is here http://archiveofourown.org/works/6734974  
> Also, much much much love to wetsammywinchester who edited out all of my glaring mistakes. Without you dear, this would be totally unreadable.

 

They drove as fast and as far as they could once they'd left the werewolf hunt in West Virginia. They were both exhausted and eager to put some space between them and the suspicious local cops back in Dixie, WV but ended up in a place wholly unfamiliar to them; Hilton Head Island, SC.

Sam blinked sleepily up at the sign for the Red Roof Inn as though it was an hallucination.

"Name brand hotel? What... What's going on, Dean?" He mumbled at his brother as he stepped out of the car and stretched.

"Well, Sammy, I was gonna stop just off I-95 but there was nothing for miles and miles. This place is like 30 miles off the highway. And I finally got here and it's all touristy and there's a beach, Savannah is just 40 minutes south and I thought, let's take a few days and have a break."

Sam rubbed his eyes in silence and turned his hazel eyes back to his brother, squinting in slight disbelief. They don't take vacations, and on the rare occasion they take time off it’s not in a place where other people take vacations. Dean began to wilt under his stare, pinking at the cheeks and rubbing the back of his neck bashfully.

"The apocalypse is coming and I dunno if this is gonna be the end of everything or the end of us or what but I thought we could take 3 days and reconnect. See if there's an easy case, sure, but have some drinks on the beach and play in the water and see just how defined we can get the tanline just above your sweet ass that I love so much."

Sam finally felt his face break out into a smile, believing that they were actually going to have this. A vacation. A hotel with no bedbugs or mold in the shower and fully functioning air conditioning.

"A king bed?" Sam used his puppy dog eyes as best he could, even pushing out his bottom lip the smallest amount. Dean stared at him, blank faced.

"Get the bags baby boy, I'll get the room." And with that, he vanished into the office while Sam got out and stretched before ducking back down into the car to grab their duffels.

An hour later, Sam stepped out of the mold-free shower and back into the main area of the suite that Dean had splurged on. It was late and they were both tired, but Dean managed to grab some food from the touristy diner down the road, grumbling all the while about over-priced, tourist bait, but Sam couldn’t care. The hot water was as strong at the end of his shower as it had been at the start, his belly was full, there was a cold beer or two waiting on his side of the California-king sized bed. Life was good.

He dropped his towel and pulled on the loose boxers that he typically only wore to bed before sliding between sheets that he wasn’t worried about the cleanliness of.  He took a long swallow of beer and watched lecherously as Dean undressed for his own shower.

“Save it, Sammy. M’tired. Have a full stomach, need a shower and a night of sleep and if you’re a good boy I’ll let you wake me up in the morning. Pervert.” Dean smirked as he sauntered into the bathroom, hips rolling all the while.

“Eh, you love this pervert.” Sam yelled in the direction of the mostly shut bathroom door, and had full intentions of rolling Dean onto his back and riding him until they were both asleep once he was out of the shower, but he fell asleep sometime between finishing his beer and Dean joining him in bed.

Sam woke up to the sound of traffic outside the hotel and sun shining through the front window where they’d forgotten to shut the blinds. Dean was already up, had already headed out to the pancake restaurant next to the hotel and grabbed them breakfast and decent coffee.

“Hey, c’mere. I had plans for this bed and m’not leaving it till we make them happen.” Sam mumbled, trying to entice Dean back into the bed with him. Dean came over, running one elegant fingered hand through Sam’s hair and tugging gently, making Sam moan and curl up towards his brother.

“That’s what I’m talking about, c’mon Dee, pull my hair and make me beg for it.”

Dean laughed, tugging harder as he swiveled his hips out of Sam’s freakishly long reach. He pulled his hand out of Sam’s hair and patted the top of his head before walking away and tossing something from his duffel at Sam’s head.

“C’mon little brother, up and outta bed. It’s eleven am, disgustingly hot and sunny outside and I wanna see the skin on the curve of your spine get all tan and sweaty.”

Sam whined from underneath the floral-print bathing suit on the top of his head. “No sex this morning?” He yanked the cloth off his head and shoved the sheets to the end of the bed. He shoved himself up off the bed and froze at the sound of a knock on the door. Dean’s messy head pushed out the door of the bathroom, eyes narrowed in suspicion at the door. Sam jumped for his gun, inside his duffel as he raised an eyebrow at his brother.

“Who knows we’re here?”

“No one! I haven’t even called Bobby yet because I don’t know how to tell him we’re taking a few days off together.”

“Housekeeping!” A cheery voice sounded from the other side of the door and Dean let out a startled laugh before ducking back into the bathroom. Sam quickly pulled off his boxers and pulled on the swim trunks as he shouted out “just a moment!” to the hotel staff on the other side of the door.

Dean grabbed the bag he’d repacked for the beach and opened the door just as Sam pulled a tee-shirt over his head. He let the housekeeper in with a wink and a smile before he grabbed Sammy’s ass and guided him out to the car.

“It’s been so long since we stayed in a normal hotel, I forgot that housekeeping shows up every day.” Sam laughed as he folded himself into the car. “I’ve forgotten...no, you know, I can’t think of a single time we’ve taken a vacation. Even when we were kids. How do we do this?”

Without turning his head to look over at his brother, Dean replied, “Well, we fill a cooler with beer and food and water and park ourselves under a beach umbrella, for my sensitive skin, while you go turn heads and frolic in the waves, getting those tan lines nice and defined. I’ll inspect them later.”

Their first ever vacation day was a total success, despite Dean’s continued grumbling about over-priced tourist trap destinations and his sunburned nose.

They fell into bed together that night, happy and smiling and kissing, but the time in the sun had taken it’s toll on them, and both brothers fell asleep quickly, much to the disappointment of both of their libidos. Dean awoke in the morning, to a warm, wet suction around his cock and weak, early morning light streaming in through the cracks in the blinds over the window.  He moaned and threw his head back into the pillow before he shoved the blankets off the bed to see Sam curled, naked, at the foot of the bed, hazel eyes wide open and focused on his face.

“Damn, Sammy, you wake me up like this and I could become a fan of vacations.” He hitched his hips upwards, fucking Sam’s face. Sam grunted and pulled off with an obscene squelching sound.

“Just trying to make sure that we get to make the most of day two of-” a tinny rendition of ‘Smoke on the Water’ cut Sam off, and he narrowed his eyes in annoyance.

“If you answer it, Dean, I swear to Christ I will leave you hanging.” He grunted, his fist squeezed tightly around the base of Dean’s still glistening cock.

“...it’s Bobby’s ring, Sammy. He’d only call if it were important.” Dean whined. He wanted Sam’s mouth back on him, but he couldn’t ignore Bobby calling. Bad things had happened the last time he’d done that. He opened his mouth to say just that, while his hand crept across the mattress towards his phone.

Sam growled up at his brother, mouthing at the wet head of his cock and waiting for Dean’s decision. When Dean decided to answer his ringing phone, Sam stood up off the bed, being sure to make a show of his naked body the whole while, and marched into the bathroom. OF course, he made sure to slam the door hard enough that, had they been in their normal kind of motel, it would have cracked the door frame. As it was, the room shook and Dean winced as he answered the phone.

Dean tried, really tried, to pay attention to Bobby. There was some kind of haunting or case or something in Savannah and Bobby needed them to look into it. However, all Dean could focus on were the loud sounds of Sam pleasuring himself in the shower. Sam was obviously projecting his voice, being louder than usual, just to get back at Dean.

Dean regretted, seriously regretted, answering the phone.

He looked sadly down at his fully soft cock, as it lay on his hip still wet with Sam’s saliva, and told Bobby that they’d go to Savannah today and check it out.

“Call you later Bobby.”

He pulled on his jeans as Sam, shiny clean and hair dripping wet, stepped out of the bathroom with a tiny towel wrapped around his hips.

“Damn, do I feel better. Nothing like a good, strong orgasm to wake you up and help you start the day on the right foot. What’d Bobby want?” He asked, trying for nonchalance but just coming off as the bitchy, younger brother.

“Don’t be like that,Sammy. C’mon! I mean, yeah okay, we are on vacation but the apocalypse is still out there. C’mon baby brother. I can make it up to you?” Dean batted his eyes and gave Sam his best seductive look. Sadly, Sam wasn’t fooled.

“Oh yeah, I get it. So, was the call about Lucifer, Michael or the apocalypse?” Sam asked mildly, not even looking in Dean’s direction.

“...No. There’s a haunting or something in Savannah that he asked us to look into.” Dean pulled a clean-ish tee-shirt over his head and sat down on the bed to lace up his boots, refusing to look up at Sam and see the anger he knew would be there.

“Yeah, not sure how you’re gonna make it up to me considering I was NAKED AND IN THE MIDDLE OF GIVING YOU A BLOWJOB WHEN YOU ANSWERED YOUR PHONE!”

Dean blinked, finally looking up at his brother and his red, angry face. He quietly finished lacing up his boots and stood up, tugging down the wrinkles at the crotch of his jeans.

“Yeah. Well, it’s a good thing I didn’t check us in as brothers, considering the whole FUCKING HOTEL knows about that now! You good? Put some clothes on Sam, I’ll go get coffee.” With the last word, for the first time since Sam started talking, Dean walked out the door.

The drive to Savannah was silent and tense, all 45 minutes of it. Bobby mentioned something about hauntings on River street, something about people being scared sick. It only ended up on his radar because one person died of a heart attack; no one had known about the man’s heart condition until they’ watched him get scared and collapse on the cobblestone street.  Bobby had no idea what was doing it, a haunting being his best guess.

Since they weren’t talking still, when they arrived at River Street, a popular tourist destination, they split up. Dean took the restaurants and Sam took the tchotchke shops. Two hours of fruitless searching for both of them, found them meeting at a daiquiri shop called Wet Willies and sitting down in the humid sunshine.

“Nothing. I mean, a few of the people heard about it and I talked to someone who watched the victim collapse but no one saw anything weird and no sign of EMF.”  Dean started, taking a long sip of something fruity and frozen.

Sam sipped at his, probably virgin, version of something else brightly colored. “I did hear something odd from a few people. They all said that the victims, especially the one who died, called out to someone in the crowd right before they were affected. That’s thin but kinda weird.”

They sat and drank in silence for a few minutes, Sam looking out over the river while Dean studied his brother. Winchesters could hold a grudge like no one’s business, and the two of them were no exception, but Dean wasn’t willing to waste precious time by fighting over something stupid. So, with that in mind, Dean went about apologizing in the only way that he knew. Bribery.

“So, River Street Sweets was having a sale and I got you something.”  He began, as he pushed a bag across the tiny metal table. Sam eyed him and the bag for a moment, saying nothing, but eventually he peeked inside the bag, and Dean knew he was mostly forgiven.

A pound of pralines and a tin He-Man lunchbox filled with saltwater taffy had Sam smiling so much that his dimples came out and Dean couldn’t resist; he leaned over and kissed the dimple closest to him.

“I think that we can forget about this-hey! Was that Jo?” Sam cut himself off mid sentence, pointing at someone who bared an uncanny resemblance to their Jo, right down to a shirt both of them thought they’d seen her wear before.

“If she’s in Savannah, why did Bobby bug us with this?” Dean wondered aloud, but Sam didn’t hear him, too busy trying to get Jo’s attention.

“Jo! Hey, JoAnna Beth Harvelle, over here!” Sam shouted and the girl turned and looked at him. Dean was watching when she smiled at them both but before she could take one step towards them, she lifted her right hand and wiped her face off. Sam fell backwards over the chair he’d stood up from and Dean jumped, shouting wordlessly. Dean blinked and checked on his brother and when he looked up, the monster was gone.

“Holy shit did you see that? You saw that, right? What the fuck was that Sammy?” Dean reached down and helped Sam up from the ground as the two of them tried to resolve what they’d seen.

“I don’t know Dean, but we are going to find out. Gather up our stuff, I need to get to a library.”

They high tailed it back to the car and found their way to the Savannah public library in short order, Sam heading instantly to the local history section and Dean, despite all the of the trouble he’d been in that morning and the apology he’d just issued to his brother, hung around the front where the cute art students were congregating and smiling at him bashfully.

After only about a half-hour of harmless flirting with the cute boys and girls of the art school, Sam found him. “Really, Dean? These kids are at least 10 years younger than you.” He admonished Dean, loving the chance to embarass his brother and make the cute girls giggle at them.

“So get this, apparently River and Bay streets in Savannah have been haunted by this thing for years, since about 1906, when a prominent Japanese family immigrated to Savannah. I haven’t been able to find out what it is, but the one thing that all the stories have in common is what we knew already, that it takes on the form of someone familiar to the person they’re haunting. I don’t even know if they’re strictly dangerous or not, a lot of Japanese monsters are just tricksters.”

Dean looked on fondly as Sam read from notes he’d made for himself. It sounded, to him, like they were almost there with the case. Just identify the monster and figure out how to kill or dispel it and they could go back to their vacation.

“Okay, so what now college boy? You wanna take the rest of the day here to figure it out or head back to the hotel… let me take you out for a fancy dinner to make up for this morning and we can start fresh tomorrow?” Dean knew full well what he wanted Sam to choose, but he was not going to tilt Sam’s opinion in one direction or the other.

“I shouldn’t reward you, but let’s head back to the hotel. I want seafood and an appetizer, drinks and dessert. In fact, I’ve looked up what the best restaurant for seafood is on Hilton Head and that’s where you are taking me.” Dean didn’t even care how much it was going to cost him; he’d do whatever it took to get Sammy back in his bed and happy.

The seafood wasn’t horrible but, the bill was intimidating, even for a seafood restaurant that was on the water. Dean paid and left a generous tip without outwardly grumbling, earning him a small, sweet smile and a caress from Sam’s ankle against his own under the table. They headed out to the valet to collect the car, looking out over the sun setting on the ocean as they waited.

“I am, you know, sorry about this morning Sammy. It’s just...much as I wanted to do this break away from everything for you I guess I feel a little…”

“Guilty? Yeah, me too, Dean. I get it. But, we need to find a balance between us and the work.” SAm agreed quietly as they stood on the dock. They both turned as they heard the rumble of the Impala’s engine.  The figure that stepped out of the car looked an awful lot like Castiel, until it handed Dean the key silently and wiped it’s face clean before turning and walking away into the darkness. Dean actually felt himself tremble a bit as he got into the car.

“Apparently it’s following us now, so we won’t have to go back into Savannah tomorrow. I’m guessing it’ll find us. And I know we dunno if they’re harmless Sammy but they sure as fuck are creepy.” Dean slammed the door and floored away from the creature.

A late phone call to Bobby taken care of while Dean showered and Sam had a few more answers. His eyes tracked Dean as he made his way through the motel room in his wet towel.

“Bobby says it sounds like a ‘faceless one’ or “Noppera-Bo”. He’s gonna do some research and get back to me in the morning; let us know if there’s a way to dispel it if it’s truly harmful or if we just have to leave it be.”

Dean nodded absently as he pulled on a pair of black boxer-briefs and a blue tee-shirt. He lay himself down across the bed and propped his head up on his crossed arms as he and Sam silently contemplated each other.

“I vote that unless there’s a monster in our hotel room, it’s an ‘us’ space.” Sam said softly, moving closer and closer to Dean as he spoke. Dean nodded his head and tilted his face up for a kiss, wrinkling his nose at the last second and turning away.

“Dude, you reek. I romanced you, I need a little courtesy back; shower and brush your teeth. I’ll be right here when you get back.” Sam laughed and nodded, pressing a kiss to the wet spikes of hair on the top of Dean’s head before climbing off the bed and pulling off his clothes, leaving a messy trail into the bathroom.

Of course, considering the way that their vacation had gone so far, Sam should not have been surprised that Dean was passed out when he came out of the shower with his teeth brushed. He smiled lovingly at his brother before gently pulling the covers out from under him and gathering him up in his arms to sleep. It wasn’t often that Sam got to ‘big spoon’ Dean without a ton of bitching from his older brother.

When Dean woke up he was alone in the room; again. Again they’d missed the chance to celebrate their mini-vacation. He was frustrated and upset that they only had one day left before they were going to have to hit the road. He stretched his back in a deep arch, absently thinking how nice it would be to have a good mattress all the time. Dean was in the shower when he heard the door open and the smell of coffee wafting through the room.

“Sammy, excellent timing. I figure I can get dressed and have coffee and then, maybe, we can go looking for this faceless thing? Though I guess we dunno how to hold it, or even if we can hold it or how to get rid of it…” He trailed off, looking up to see the body of his brother with a blank face standing in front of him.

Hackles instantly up,thinking how dare this thing impersonate his Sam, Dean studied it. Creepy, yes. Intimidating, no. He supposed that someone else might find it scary to see a loved one missing their face but between the apocalypse looming and the fact that he had a name for this thing, it did no more than get his “big brother, protective” dander up.

“So I’m guessing you can’t talk to me, what with the no face and all?” He mused aloud, wondering if the coffee this thing brought was safe. It dipped it’s head towards him in what he assumed was a nod of agreement.

“I’d like to ask you what you want but that’s useless. I gotta say, it’s kinda nice being able to objectify Sammy’s body without his mouth running all the time. Though, the things he can do with his mouth make it worthwhile. So I guess that means you gotta go. Need my brother back now.” As though the words had summoned him, Sam burst through the door and took in the scene at a glance. They nodded at each other, each taking small steps to effectively surround the monster. Despite it’s lack of face, however, it saw and catalogued their intentions quickly and before they were in position. It jetted out the slightly open door and vanished into thin air.

“Well shit. Looks like we probably can’t trap it at all. So, it can impersonate anyone, it can move fast and vanish into thin air. Doesn’t really bode well for us getting rid of it, does it?” Dean mused aloud, subtly looking SAm up and down to make sure that he was okay.

“Actually, Bobby called when I was getting coffee and told me how to get rid of it, though honestly, the lore says they’re totally harmless. Just nuisances, really. We have to reflect it’s blank face back onto itself in a silver mirror. Don’t we have one of those in the trunk?” Sam asked, already on the move out to the car but Dean reached out and grabbed his arm to stop him.

“Did anything happen while you were out” Did it take a bite out of you or anything?” Sam smiled and leaned down to kiss his brother, a deep, drugging kiss that had Dean wanting to pull SAm over to the bed and spend the day naked. Both pulled out of the kiss at the same time, matching smiles on their swollen lips.

“Nah, but you’re cute when you’re worried about me, I ever tell you that before?”

Dean sputtered indignantly as he pulled the door closed behind him and followed Sammy out to the Impala. “I am never cute!”

Sam laughed in his face for that, popping the trunk open and digging for the mirror that he knew was in there. He kissed his brother’s stubbled cheek. “You’re adorable. C’mon, let’s go.”

IN the end, dispelling the monster was anti-climactic. They floundered around Hilton Head for the day, walking around the beach and going into overpriced shops, always on the lookout for someone familiar. When they stopped for lunch at a pizza place, Ash was the one who served them, but the creature vanished before they could flash the mirror at it.

It was nearing time for dinner when they headed into the local Walgreens to restock their sadly depleted first aid kit when they finally got it. They were standing in line at the pharmacy counter, Sam behind Dean who had the mirror in his back pocket. When the person at the counter turned around, it was Bobby’s grizzled face looking back at them before it walked away. Sam snatched the mirror and ran after it, waiting for it to turn and blank it’s face before he opened the small mirror compact and showing the monster it’s own reflection just outside in the parking lot.

“You get it?” Dean asked calmly when he met Sam near the Impala, bags of medical supplies on his arms.

“Yeah, it’s gone. We ready to go?”

Dean put the bags in the car and reached into one, pulling something out and placing it in Sam’s hand. “Actually, we have one more night in the hotel.” He said absently, waiting for Sam’s reaction to the vibrating, jelly cock ring that he’d just place in his outstretched palm. Sam looked down and flushed.

“Since when does Walgreens sell sex toys?” He squeaked, causing an older couple to turn and look at him, scandalized.

“Dunno, you comin’?” Dean revved the engine for effect and waited as patiently as he could for Sam to get into the damn car.

IN the end, the vacation wasn’t a total loss.  Though he’d only been out on the beach for one day, Sam’s tanline was nice and pronounced at the top curve of his ass. Dean blew sam up against the door of their hotel room before fucking him into the mattress and then taking him again in the shower before they fell asleep. When Dean woke up, Sam was riding him, ensuring that he would feel every single bump in the road that day.

They checked out on time, with love bites on their necks, bruises on their hips from gripping too tight and smiles on their faces. A successful Winchester vacation: monster slayed, people saved and good sex had by all.

  


**Works inspired by this one:**

  * [Art for 'A Successful Winchester Vacation'](https://archiveofourown.org/works/6734974) by [stormbrite](https://archiveofourown.org/users/stormbrite/pseuds/stormbrite)




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